Getting back into the dating world after years in a long-term relationship can feel like stepping into a whole new universe. The rules have shifted, dating apps reign supreme, and the charm that once worked a decade ago might now fall flat. It’s no wonder that re-entering the scene can be a bit overwhelming.
That’s exactly what one man experienced when he recently dipped his toes back into dating—and ended up with a situation he never saw coming. After planning a casual first date, he was caught off guard when his date asked him to cover the cost of the babysitter she’d hired for the evening.
Confused and unsure if this was a common expectation or totally out of line, he turned to Reddit for answers. Below is the full story, along with some strong opinions and helpful insights from fellow users who’ve seen it all.
This man wasn’t sure what would happen on his first date post-divorce

But he certainly wasn’t expecting the woman to ask him to pay for her babysitter











Readers assured the father that her request was not normal, and many encouraged him not to schedule a second date
















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